U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H14O4.2Na
Molecular Weight 232.1846
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISODIUM AZELATE

SMILES

[Na+].[Na+].[O-]C(=O)CCCCCCCC([O-])=O

InChI

InChIKey=QFYNUCAKHMSPCY-UHFFFAOYSA-L
InChI=1S/C9H16O4.2Na/c10-8(11)6-4-2-1-3-5-7-9(12)13;;/h1-7H2,(H,10,11)(H,12,13);;/q;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula C9H14O4
Molecular Weight 186.2051
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/?term=2114832 https://www.ncbi.nlm.nih.gov/pubmed/18803456

Azelaic acid, a naturally occurring saturated dicarboxylic acid found in wheat, rye, and barley, possesses antimicrobial activity, affects keratin production, and reduces inflammation. One of the brand name for azelaic acid is FINACEA,Gel, 15% is indicated for topical treatment of the inflammatory papules and pustules of mild to moderate rosacea. Although some reduction of erythema, which was present in patients with papules, and pustules of rosacea occurred in clinical studies, efficacy for treatment of erythema in rosacea in the absence of papules and pustules has not been evaluated. Rosacea is a common skin condition thought to be primarily an inflammatory disorder. Neutrophils, in particular, have been implicated in the inflammation associated with rosacea and mediate many of their effects through the release of reactive oxygen species. Many effective agents for rosacea, including topical azelaic acid have anti-inflammatory properties. Azelaic acid per se has multiple modes of action in rosacea, but an anti-inflammatory effect achieved by reducing reactive oxygen species appears to be the main pharmacological action. A possible mechanism of action for azelaic acid in the human epidermis includes its possibility to inhibit tyrosinase and of membrane-associated thioredoxin reductase enzymes, this enzyme is shown to regulate tyrosinase through a feedback mechanism involving electron transfer to intracellular thioredoxin, followed by a specific interaction between reduced thioredoxin and tyrosinase.

CNS Activity

Curator's Comment: Azelaic acid is capable of crossing the blood-brain barrier: its concentration in the cerebrospinal fluid is normally in the range of 2-5% of the values in the serum.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P14679
Gene ID: 7299.0
Gene Symbol: TYR
Target Organism: Homo sapiens (Human)
2.73 mM [Ki]
125.0 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
FINACEA

Approved Use

FINACEA® (azelaic acid) Gel, 15% is indicated for topical treatment of the inflammatory papules and pustules of mild to moderate rosacea. Although some reduction of erythema which was present in patients with papules and pustules of rosacea occurred in clinical studies, efficacy for treatment of erythema in rosacea in the absence of papules and pustules has not been evaluated.

Launch Date

2002
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
112 ng/mL
1 g single, topical
dose: 1 g
route of administration: Topical
experiment type: SINGLE
co-administered:
AZELAIC ACID unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
136 ng/mL
1 g 2 times / day steady-state, topical
dose: 1 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
AZELAIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
613 ng × h/mL
1 g single, topical
dose: 1 g
route of administration: Topical
experiment type: SINGLE
co-administered:
AZELAIC ACID unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
686 ng × h/mL
1 g 2 times / day steady-state, topical
dose: 1 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
AZELAIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12 h
1 g single, topical
dose: 1 g
route of administration: Topical
experiment type: SINGLE
co-administered:
AZELAIC ACID unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Combination azelaic acid therapy for acne vulgaris.
2000 Aug
Characterization of novel di- and tricarboxylic acids in fine tropical aerosols.
2001 Apr
Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction.
2001 Feb
["Cleansing, topical treatment, oral administration". Controlling acne].
2001 Jul 26
The modern age of acne therapy: a review of current treatment options.
2001 Sep-Oct
Bioactive constituents of the seeds of Brucea javanica.
2002 Aug
Sensitive and accurate quantitation of monoepoxy fatty acids in thermoxidized oils by gas-liquid chromatography.
2002 Dec 20
Total synthesis of (-)-minquartynoic acid: an anti-cancer, anti-HIV natural product.
2002 Jul 25
[Studies on chemical constituents of root of Cichorium intybus].
2002 Mar
Cocrystal structures of diaminopimelate decarboxylase: mechanism, evolution, and inhibition of an antibiotic resistance accessory factor.
2002 Nov
Unknown peaks in GC-MS analyses of Guthrie cards blood samples might be the result of sample contamination by the black markings of the card.
2002 Oct
Burkholderia cepacia complex genomovars: utilization of carbon sources, susceptibility to antimicrobial agents and growth on selective media.
2003
Transdermal penetration of topical drugs used in the treatment of acne.
2003
Guidelines for the management of acne vulgaris in adolescents.
2003
Topical treatment in acne: current status and future aspects.
2003
Separation of homologues and isomers of linear alkylbenzenesulfonates by capillary electrophoresis with sodium dodecyl sulfate, carboxylic acids and bile salts.
2003 Feb
Urotropin azelate: a rather unwilling co-crystal.
2003 Feb
Management of acne.
2003 Jan
Atmospheric pressure mass spectrometry: a new analytical chemical characterization method for dissolved organic matter in rainwater.
2003 Jan 1
Gas chromatography-mass spectrometry profile of urinary organic acids of Wistar rats orally treated with ozonized unsaturated triglycerides and ozonized sunflower oil.
2003 Jan 15
Efficacy and safety of azelaic acid (15%) gel as a new treatment for papulopustular rosacea: results from two vehicle-controlled, randomized phase III studies.
2003 Jun
Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modified protein.
2003 Jun
A comparison of 15% azelaic acid gel and 0.75% metronidazole gel in the topical treatment of papulopustular rosacea: results of a randomized trial.
2003 Nov
Analgesic effects of intra-nasal enkephalins.
2003 Sep
Azelaic acid (Finacea) for rosacea.
2003 Sep 15
Optimal management of recalcitrant disorders of hyperpigmentation in dark-skinned patients.
2004
Diltiazem-induced hyperpigmentation.
2004 Apr
Evaluation of the antibacterial efficacy of diesters of azelaic acid.
2004 Apr
Rosacea. An overview of diagnosis and management.
2004 Dec
Medical treatment of rosacea with emphasis on topical therapies.
2004 Jan
Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov.
2004 May
Aerosol products, mechanisms, and kinetics of heterogeneous reactions of ozone with oleic acid in pure and mixed particles.
2005
Considerations for treating acne in ethnic skin.
2005 Aug
Chemical modification of proteins during peroxidation of phospholipids.
2005 Jul
Lipid-derived modifications of plasma proteins in experimental and human diabetes.
2005 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Evidence-based dermatology.
2005 Mar
Present and future rosacea therapy.
2005 Mar
Red facial rash with "granitos".
2005 Sep
[Rosacea. Clinical features, pathogenesis and therapy].
2005 Sep
The evolution of azelaic acid.
2006 Feb
Patents

Sample Use Guides

Apply and gently massage into the affected areas on the face twice daily (morning and evening). Patients should be reassessed if no improvement is observed upon completing 12 weeks of therapy.
Route of Administration: Topical
In Vitro Use Guide
Using a clonogenic assay in vitro, it has been shown that exposure to azelaic acid (1-100 mM) for 24 hours has a dose-dependent effect on the survival of the colony-forming ability of murine (B16) and human (HMB2, and SK23) melanoma cells as compared with a non-melanotic non-tumoral Chinese hamster cell line (CHO). Both human cell lines were more sensitive to the diacid than the murine cells, and the HMB2 cells were more sensitive than the SK23 cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:09:05 GMT 2023
Edited
by admin
on Sat Dec 16 20:09:05 GMT 2023
Record UNII
0P4H8NH3UJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DISODIUM AZELATE
INCI  
INCI  
Official Name English
DISODIUM NONANEDIOATE
Systematic Name English
SODIUM AZELATE (2:1)
Systematic Name English
NONANEDIOIC ACID, DISODIUM SALT
Common Name English
NONANEDIOIC ACID, SODIUM SALT (1:2)
Common Name English
DISODIUM AZELATE [INCI]
Common Name English
AZELAIC ACID, DISODIUM SALT
Common Name English
Code System Code Type Description
CAS
27825-99-6
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
NON-SPECIFIC STOICHIOMETRY
MESH
C010038
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID40889659
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
CAS
17265-13-3
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
FDA UNII
0P4H8NH3UJ
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
PUBCHEM
159815
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
RXCUI
2117384
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
241-298-4
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE